Wine Tasting in Montepulciano area

I’ve found Google Maps to be a good starting point. I look in the area where I’m going to be, identify a few places, then look for the winery’s official website and or any on-line reviews (e.g., Trip Advisor or other travel sites like this one). Most places have different options for tasting, tours, and food and they almost always highly recommend (or require) reservations. Another option is to sign up for a private or semi-private tour. A lot of the towns you mentioned have wine shops that do tastings, as well.

We visited Montepulciano a number of years ago on a culinary tour. Our tour guide took us to Crociani Winery. We all enjoyed our tasting at the lovely winery. Wonderful wines from the region! http://www.crociani.it/index.en.php

We have used this as a reference over several years before Covid. With that in mind, call before heading out to explore. Reservations are needed for most.

https://www.winewordswisdom.com/travel_itineraries/southern-tuscany-wine-tour.html

There are a number of sources that will identify the wineries. We once spent a week visiting two to three wineries each day. We found that advance reservations were critical and a fee was involved. We did find a couple that offered a three to five course luncheon with paired wines. Great experience but it was expensive. The wine tasting experience is not as casual as you generally find in CA or other wine states. For us and the wineries we visited, a car was necessary. There are some that are set up to the bus tourist trade but we found them to be less satisfactory.

There's a winery a bit north and east of Montepulciano, sort of on the way to Cortona, that has a really nice paired tasting lunch we did in 2018. It's called Avignonesi, and they're famous for their Vin Santo. They provide a nice tour of their vineyards and facility, a really great lunch and are pretty generous with their pours throughout the process. They even went off-script and broke out the grappa at the very end of the meal. : )

Well, these territories are really full of high-level wineries. There are some really well-known such as Contucci or De Ricci. First of all, I would suggest you check the TripAdvisor lists. I think it gives you some good picks. But consider also to visit the Chianti, like Castellina, Greve or Castelnuovo Berardenga. A really beautiful place with a lot of famous wineries as well, also visited by well-known people in recent years. And of course, Chianti Classico wine is a must-try if you visit Tuscany.